Water → HCID 86677243, compound

HRID 1842718Notes

Reaction equation

HRID 1842718 reaction equation
[Cl:1][C:2]1[C:3]([C:38]2[CH:39]=[N:40][N:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=23)=[N:4][C:5]([NH:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][C:12]([N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:34])[C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])[CH2:19][CH2:18]3)=[C:11]([N+:35]([O-])=O)[CH:10]=2)=[N:6][CH:7]=1.[NH4+].[Cl-].O>C(O)C.[Fe]>[NH2:35][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[N:4]=[C:3]([C:38]3[CH:39]=[N:40][N:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=34)[C:2]([Cl:1])=[CH:7][N:6]=2)[C:14]([O:15][CH3:16])=[CH:13][C:12]=1[N:17]1[CH2:18][CH2:19][N:20]([C:23](=[O:34])[C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH3:25])[CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 71270463HCID 71270463, compound2×

Product 1

HCID 86677243HCID 86677243, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-tert-butyl N-[1-(4-{4-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-5-methoxy-2-nitrophenyl}piperazin-1-yl)-1-oxopropan-2-yl]carbamate (Intermediate 60, 100 mg, 0.15 mmol), iron (51.4 mg, 0.92 mmol) and NH4Cl (5.74 mg, 0.11 mmol) was heated at reflux in ethanol (3 mL) and water (1 mL) for 1 h. Purification by ion exchange chromatography, using an SCX column and eluting with 7M methanolic ammonia provided material that was further purified by FCC, eluting with O-5% CH3OH in CH2Cl2 to give the title compound (65 mg, 68%) as a yellow solid; m/z: ES+ MH+ 622.58.

Workup

  1. temperaturewas heated
  2. customPurification by ion exchange chromatography
  3. washeluting with 7M methanolic ammonia provided material that
  4. customwas further purified by FCC
  5. washeluting with O-5% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-31903c60722d435aba9c2f7af182d298
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

Loading…